D-Leucic acid (YMDB02318)

Identification

YMDB ID

YMDB02318

Name

D-Leucic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Leucinic acid, also known as leucate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Based on a literature review a significant number of articles have been published on Leucinic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-2-Hydroxyisocaproate
(+)-2-Hydroxyisocaproic acid
(+)-a-Hydroxyisocaproate
(+)-a-Hydroxyisocaproic acid
(+)-alpha-Hydroxyisocaproate
(+)-alpha-Hydroxyisocaproic acid
(2S)-2-Hydroxy-4-methylpentanoate
(2S)-2-Hydroxy-4-methylpentanoic acid
(S)-(-)-2-Hydroxyisocaproic acid
(S)-2-hydroxy-4-methyl-Pentanoate
(S)-2-hydroxy-4-methyl-Pentanoic acid
(S)-2-Hydroxyisocaproate
(S)-2-Hydroxyisocaproic acid
(S)-Leucate
(S)-Leucic acid
2-Hydroxy-4-methylvaleric acid
6-methyl catacid
Hydroxyisocaproate
Hydroxyisocaproic acid
L-2-Hydroxy-4-methylpentanoic acid
L-2-Hydroxy-4-methylvalerate
L-2-Hydroxy-4-methylvaleric acid
L-2-Hydroxyisocaproate
L-2-Hydroxyisocaproic acid
L-a-Hydroxyisocaproate
L-a-Hydroxyisocaproic acid
L-alpha-Hydroxyisocaproate
L-alpha-Hydroxyisocaproic acid
L-Leucate
L-Leucic acid
S-2-Hydroxy-4-methylpentanoate
S-2-Hydroxy-4-methylpentanoic acid
2-Hydroxyisocaproic acid
2-Hydroxyisohexanoic acid
alpha-Hydroxyisocaproic acid
Leucic acid
2-Hydroxyisocaproate
2-Hydroxyisohexanoate
a-Hydroxyisocaproate
a-Hydroxyisocaproic acid
alpha-Hydroxyisocaproate
Α-hydroxyisocaproate
Α-hydroxyisocaproic acid
Leucate
Leucinate
alpha-Hydroxyisocaproic acid, (R)-isomer
alpha-Hydroxyisocaproic acid, calcium (2:1) salt, (S)-isomer
alpha-Hydroxyisocaproic acid, monosodium salt
alpha-Hydroxyisocaproic acid, (S)-isomer
2-Hydroxy-4-methyl-valerate
2-Hydroxy-4-methyl-valeric acid
2-Hydroxy-4-methylpentanoate
2-Hydroxy-4-methylpentanoic acid
2-Hydroxy-4-methylvalerate
a-Hydroxy-iso-caproate
a-Hydroxy-iso-caproic acid
alpha-Hydroxy-iso-caproate
alpha-Hydroxy-iso-caproic acid
DL-2-Hydroxy-4-methylpentanoate
DL-2-Hydroxy-4-methylpentanoic acid
DL-2-Hydroxyisocaproate
DL-2-Hydroxyisocaproic acid
DL-a-Hydroxyisocaproate
DL-a-Hydroxyisocaproic acid
DL-alpha-Hydroxyisocaproate
DL-alpha-Hydroxyisocaproic acid
DL-Leucate
DL-Leucic acid
Leucinic acid

CAS number

13748-90-8

Weight

Average: 132.1577
Monoisotopic: 132.07864425

InChI Key

LVRFTAZAXQPQHI-UHFFFAOYSA-N

InChI

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)

IUPAC Name

2-hydroxy-4-methylpentanoic acid

Traditional IUPAC Name

leucate

Chemical Formula

C₆H₁₂O₃

SMILES

CC(C)CC(O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Alpha-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy fatty acid (CHEBI:59783 )
branched-chain fatty acid (CHEBI:59783 )
Hydroxy fatty acids (LMFA01050381 )

Physical Properties

State

Solid

Charge

Melting point

78-80 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	124 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.51 m³·mol⁻¹	ChemAxon
Polarizability	13.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0883a44db52a6c25fe99	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-02gc-9440000000-7fffd162011678b17f4a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014r-9000000000-5e0d546d1d0e6bb8c48c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9100000000-ed29dea8a5c4015ec5f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-8900000000-44e1b9618ac09f8f20b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001r-7900000000-7ab0c9dc80e61fa580c9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001r-7900000000-7ab0c9dc80e61fa580c9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9100000000-b13176bdf03a9a3860aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-702157a92667487bd5f6	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-7900000000-d13b28975eefc974bbca	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-9200000000-aaa07e44b97e9617d7f1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-931176b5fcc7e8bde29c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-c818e3e6474333b25326	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053i-9200000000-bd611de2f2748fe8a7fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ap0-9000000000-4e37e159ea3117d8a516	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9700000000-a7d0b1ce1c211b31bc0d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-9100000000-504826b66e199a65ef09	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-ccecb4a470c359949fec	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-3019a9d0620e7da01963	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-e587d44396e53f2409fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-457ece1d510dad645c89	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	58992
HMDB ID	HMDB00746
Pubchem Compound ID	83697
Kegg ID	Not Available
ChemSpider ID	83753
FOODB ID	FDB022171
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0x9df0c6f0>